Jimmy and his guest, investigative reporter Leah of The Leah Files, examine allegations that Shawn Ryan’s public advocacy for privacy and criticism of the establishment conflict with his reported investments in surveillance, defense technology, and companies such as Palantir and Flock. They question whether Ryan’s investments, his reported discussions about accepting major financial backing, and allegations that his team restricted discussion of certain investors create potential conflicts of interest, while criticizing his responses as failing to address the central concerns. The two also discuss Glacier, a privacy-focused app associated with Ryan, raising questions about its burner-number feature, metadata collection, third-party provider Twilio, and how user information might be handled in response to government subpoenas. Jimmy argues that financial ties to defense and surveillance companies deserve greater transparency, particularly when a media personality presents himself as anti-establishment, and questions whether commercial relationships could influence editorial independence. Leah on Twitter: https://twitter.com/leahfiles Leah’s Substack: https://substack.com/@theleahfiles Become a Premium Member: https://www.jimmydore.com/premium-membership Go to a Live Show: https://www.jimmydore.com/tour Subscribe to Our Newsletter: https://mailchi.mp/jimmydorecomedy/ytlivestreams LIVESTREAM & LIVE SHOW ANNOUNCEMENTS: Email: https://mailchi.mp/jimmydorecomedy/ytlivestreams Twitter: https://twitter.com/jimmy_dore Facebook: https://www.facebook.com/JimmyDoreShow Instagram: https://www.instagram.com/thejimmydoreshow WATCH / LISTEN FREE: Videos: https://www.jimmydore.com Podcasts: https://www.jimmydore.com (Also available on iTunes, Apple Podcasts, Spotify, Google Podcasts, or your favorite podcast player.) ACCESS TO FULL REPLAYABLE LIVESTREAMS: Become a Premium Member: https://www.jimmydore.com/premium-membership SUPPORT THE JIMMY DORE SHOW: Make a Dona